Rock Bottom
by GrapplingHook
Summary: When Dipper loses everything he cares about, his life takes a dramatic turn for the worse. He'll learn that you never really know how bad things were until you see from the perspective of someone in the same position, and that sometimes it takes that interpersonal bond to fully move on from your past and right your wrongs. (Three-Shot.)
1. Homeless

Thirty years is a long time to wait for a sibling. Too long for Dipper Pines.

Weirdmaggedon came and passed, like Christmas Day or a warm Summerween night. Ford, Stan, and Dipper managed to 'defeat' Bill with the help of some friends. The whole day was really just a blur to him, lost within the thirty years of pain, suffering, and emotional agony. Bill had taken Mabel to who knows where, it didn't really matter. There was a chance she was dead. A chance she was subjected to torture for the rest of her life. None of it mattered. She was gone.

They tried to bring her back. Incantations, rebuilding the portal, and even attempting to summon Bill for one last deal were all subject to testing. But the spells never worked. The portal never flashed. The demon never came. They tried and tried, using as much brain power the three of them and Soos could muster. At one point they even tried to fix McGucket's mind, to no avail.

Five years passed, along with Ford, and then Grunkle Stan just two months later. Dipper was left alone with the shack. His parents thinking that their two children were learning valuable business skills and adult values. The former couldn't be any further from the truth. The latter, an unfortunate reality.

Dipper and Soos made due, running the shack just a few days a week to provide themselves with enough money for electricity, water, and food. Wendy had gone off to school to become an environmental scientist, ironically finding ways to cut down on deforestation with some small firm in Portland.

The days of waiting took their toll on Dipper. Stress ate him from the inside out. He lost weight because he constantly ignored the need to eat while he tried to get the portal to work from within the basement. He went long periods without shaving; Soos would have to trim his beard and mustache at night after he passed out from exhaustion. His mental state decreased day by day. His memory lapsed on occasion, paranoia pounded on his brain and dilated his pupils, and depression struck his heart from deep within. Until one day, his progress with the portal came to a halt, changing the path of his life forever.

Dipper had gone out with Soos to the hardware store, off to retrieve a few nuts and bolts. That's when a large 8.8 magnitude earthquake stuck in central Washington, and the aftershocks were felt all across the northwest. The old infrastructure of the shack couldn't deal with the shear force of the earthquake, and the wooden supports fell, crumbling on top of the foundation. The entirety of the Mystery Shack was destroyed. As was the portal Dipper had nearly completed. The past ten years had gone to waste. Dipper lost it all.

The two moved into a motel that night. All Dipper was left with was the shirt and vest on his back, a picture of him and Mabel at age twelve, and thirteen dollars. Overnight he ditched Soos and used the rest of his money to catch a bus to Portland. That bus broke down on the side of the highway, five miles outside of the city, forcing the passengers the exit the bus on top of an overpass. The new bus arrived, and the passengers were required to show their tickets to board. When it was his turn, Dipper reached into his pocket, grabbing both his ticket and the picture of him and Mabel.

A strong wind blew, knocking the ticket, and the picture, out of his hands and over the railing. The photograph floated down, landing in the back of a garbage truck. Dipper snapped. He rushed down the highway, screaming at the speeding cars to stop. No one did. Dipper made his way to Portland by walking on the side of the highway, ignoring the vehicles ferociously honking at him. With no money, no motivation, and no sanity left in his mind. He was at rock bottom with nowhere to go, or no one to turn to but the shattered inner workings of his mind. He was broken.

* * *

 ** _20 years later_**

A man, whose bones are defined visibly through his pale skin, waits in line outside of a building with dozens of other people hoping to get inside, at least for tonight. The man mumbles incoherently to himself, his frail fingers twitching as if he were counting how many people stood in front of him. His clothes are tattered, torn on both sleeves. His only possessions are a half-eaten bag of peanuts that he scavenged from a dumpster outside an apartment complex, and a dirt-caked blanket a young child gave to him eight years ago. The line moves forward, and so does the man. He hobbles on the concrete as he steps towards the door. His left foot is protected only by that of a black sock that had originally been white. His right foot is covered by a dirty boot, his sock exposed through a hole in the top of the shoe. The man fidgets some more, this time stroking his long gray beard at a quick pace.

The cold swirling wind blows against his back, which is covered by a light windbreaker with a broken zipper. Beneath that, nothing but an orange t-shirt two sizes too big. Winter is upon the Pacific Northwest at this time of November, bringing a package of fluffy snow and blistering cold with it. The man moves along with the line once more as the tender voice of a woman becomes audible. She checks each person, man, woman and child, for signs of drugs with a quick result blood test. Those who were clean would be allowed to spend the night on one of the cots set up in rows of three, and columns of twenty in the small building. If any trace of drugs were found in your system, there was no sympathy shown to the fact that you would not be allowed admission.

It's his turn.

The man limps forward and places out his palm to be pricked. However, the lady stops him. She speaks loudly, cupping her hands over her mouth to project her voice as if he isn't there. "We're filled up for the night, sorry." Ignoring the man, the woman walks into the building and slams the door behind her.

He stands in disbelief as white flakes fall from the sky, and begin the process of littering the streets with a crystalline blanket. He cries out. His yellow teeth are exposed, minus the exception of a molar and two canines that had fallen out long ago and were now filled with dark voids. He slaps the wooden door with open palms as the rest of the homeless scatter about to take cover.

 _Click._ The door locks from within. The man slaps harder with his browned fingertips. He violently yells incoherent noises at the lady on the other side. However, his arms grow weak quickly, and he finds himself traveling south on SE Stark street.

The roads are quiet at this time of night. Only the occasional car drives by with their windshield wipers swishing back and forth, back and forth, back and forth. The tires crunch and flatten the snow underneath, leaving a trail of groves and ridges imprinted in its wake. The street lamps illuminate portions of the road, showcasing the falling flakes before they pile up on the concrete sidewalk. The dark spots of the road provide an aura of calmness, the flakes invisible to the naked eye from far away.

The buildings on both sides are mostly dark. A shifty looking car dealership, an abandoned plaza, and an apartment complex subject to demolition, all rest under the cover of the moon. They match the surrounding darkness with their own absence of light, expanding the night's grip of the shabby streets of Portland's worst neighborhood. The stop light half a block away changes from red to green despite no cars being present at the intersection. The only other source of light, besides the rows upon rows of stop lights and street lamps, comes from the flickering sign of a McDonald's on the opposite side of the intersection.

The man treads across the four lane street, unable to feel the blistering cold snow against his frostbitten foot. One car sits in the parking lot of the fast-food restaurant. The chains had switched to touch screen ordering, eliminating the need for cashiers. At night, a single cook and a janitor held down the fort. The man limps into the parking lot. He glances up at the sign and continues walking with his head turned. _Happy Thanksgiving,_ it read in its bold black letters against the pale-yellow background.

He approaches the door and pushes. It doesn't budge. He feels his hand around, still staring at the large neon-yellow 'M' as he does so. He yanks the door open and ignores the _No shoes, No shirt, No service_ sign. He steps inside and is warmed up by the heat blasting through the vents above. His head twitches as he scans around the seating area. There's no one in sight. Christmas music echoes loudly throughout the building as the cook blares his old-school IPhone '30 as loud as possible to pass the time.

The man quietly hobbles over to a booth towards the front of the restaurant, as far away from the kitchen as possible. He lies down against the hard red plastic bench, and covers himself with his stained blanket. He coughs and curls up as much as possible to fit in the seat. With his shoes hanging over the edge, he gently closes his eyes to rest for the night.

His sleep is short lived.

He awakes from his slumber a few minutes later by a teenager and his friend. They laugh as they squirt a bottle of ketchup in his direction. The red stream oozes onto his clothes, and entangles his beard with spots of red. The man flails his arms in the direction of the kids, swiping at both of them with his unclipped fingernails. They throw the half-filled bottle at him and continue to gawk as they taunt the man. The blaring saxophone from a Harry Connick Jr. Christmas song ceases as the music is turned off. The two teens spin around to see the janitor pounding a large silver wrench in his palm. Without saying a word, the kids scatter in fear, rushing out of the restaurant faster than they came in.

The janitor, in his 40's, examines the man with tired eyes as he sits on the bench covered in ketchup. Placing the wrench into his pocket, he silently leaves. A few minutes pass until the janitor comes back to the dining area. When he returns he brings a burger, apple slices, and a bottle of water with him. The janitor places them on the table in front of the homeless man who had just finished wiping the ketchup from off his face with his dirty blanket.

The janitor slides into the seat across the table and stares at the homeless man with brown eyes, waiting for him to start eating. The janitor turns and gazes out the window, the mesmerizing snow gently floats down onto the parking lot below. "You know... I used to be in the same situation nearly a decade ago." He sighs, not bothering to turn to the homeless man who slowly reaches for the food, mainly because he can see via the reflection in the window. "I came here with nothing... I tried to find an old friend, and a job. Turned up empty on both." The homeless man opens and chugs the crisp clean bottled water he is unaccustomed to. The janitor presses on with his story. "I fell into depression, lived in vacant homes for a while until I was out on the streets. That cycle continued for ten or so years. I was at rock bottom." He pauses and notices the homeless man reaching out towards his shoulder to comfort him. He doesn't flinch. "I... I attempted suicide." The janitor wipes his tearing eyes with his sleeve. "Jumped off the Ross Island Bridge... figured it'd be a far enough fall to be quick and painless unlike the previous fifteen years of my life. I missed the rocks though..." His voice shakes and quivers, as his throat becomes numb. "Drowned instead. My friend found me downstream and performed CPR. Then she got me the help I needed for five long years." The janitor turns away from the window and glances at the man on the other side of the table. "She got me this job, to regain my footing... I- I want to repay the favor." He looks down at the floor and shakes his head in disappointment. "Not because I have to. Because I want to." He raises his head and smiles. "You have a name?" The janitor asks, extending his hand out in good faith.

The homeless man seemingly contemplates accepting the offer, perplexingly staring at the Janitor's hand like it's a foreign object. The homeless man crawls out of the booth and limps away, as if the entire conversation had never happened. The janitor gapes in amazement as the homeless man walks right out of the restaurant, and back into the cold streets.

A deep voice from the kitchen snaps the janitor's attention away from the homeless man. "Hey Dipper, can you help me with the inventory check?" The janitor faces back towards the window where the homeless man last was.

But no one is there.


	2. Loveless

**A/N: This chapter was longer than I originally planned, so this story will have three chapters instead of two. Enjoy! (Make sure to fave, follow and review. :)**

* * *

 _ **6 Hours Later**_

"I'll catch ya later Dipper." The cook says as he sticks head halfway outside of the employee exit in the back of the McDonald's. "Have a good turkey day!" The cook bundles up in his jacket and hustles out the door to his snow covered car resting idly in the parking lot. Dipper sprouts a feign smile while he closes the door for him. He steps over to the locker area, snags his backpack, and makes his way to the bathroom.

The morning crew had arrived for their shift ten minutes ago, signaling the start of Dipper's daily routine. He walks to the employee restroom, enters, and locks the red door behind him. Dipper takes a deep breath as he steps up to the sink and turns the faucet on. He ignores his reflection in the mirror while he rinses his hands with soap and hot water. Dipper dries his hands on his janitorial uniform, and with the faucet still running, he reaches into his bag to pull out a clean pair of clothes. The steam from the sink fogs up the mirror as Dipper places a blue sweater and tan khakis neatly on a baby changing station sitting against the opposite wall. He stuffs his hands into the knapsack again, this time pulling out three bottles of pills and a plastic Ziploc bag that enveloped a single joint.

One by one Dipper opens each prescription bottle, shakes a pill out, and with no water, swallows it whole. His face clenches up after each gulp as if he had taken a shot of strong whiskey that burnt his throat while it traveled to his stomach. Dipper downs his last capsule and tosses the bottle back into the backpack. The fog from the near boiling hot water reaches the smoke detector and protects it with a layer of mist. Dipper undresses. He actively tries to prevent the uniform from touching the scummy bathroom floor as he slips his legs out of each pant leg. He succeeds in his endeavor and stuffs the ensemble into the backpack.

Dipper lifts the plastic baggie in front of his face and gazes at the joint in front of him. He shakes his head and trots over to the toilet. He contemplates flushing it down the drain. But something holds him back. Dipper succumbs to the pressure and pulls it out of the bag. He bends down to his knapsack, pulls out a lighter, and snaps the flame on.

 _ **10 Minutes Later**_

Dipper hacks out a cough as he exits the bathroom in his new getup. His blue sweater has a small crimson stain on the sleeve, and his khakis are dirtied with light brown lines from landing on the bathroom floor. He squeezes by customers entering the fast-food restaurant and ignores their shrill "Happy Thanksgiving" welcome. Dipper rushes out to the parking lot where the cold meets him with a grand slap in the face. The frigid wind cuts right through his sweater and gnaws at his skin as he hustles to the corner of the parking lot where a Chevy Avalanche, Limited Edition, waits patiently for him. Exhaust smokes from the rear tailpipe as he approaches the shiny red truck. The mixed smell of gasoline and French fry grease fills the air around him, wrapping his nose in a putrid blanket.

He reaches out for the passenger side door and pulls on the ice-covered handle. It's locked. _Click._ Dipper tries again. This time the door swings open and he lifts himself into the vehicle. He slams the door shut and stomps his shoes on the carpeted floor to knock off the loose snow. A voice startles him as he reaches for his seat belt. "Hi!" Dipper glances over the headrest and grins at the five year old girl joyfully beaming at him with two missing front teeth. She had her mother's bright red hair, her glittering green eyes, and generally laid-back attitude.

Dipper drops his bag on the floor and swivels in his seat to face the front. "Hey Lilly." He reaches over the seat and holds a closed fist a couple of feet in front of her. She bumps it back with a fake explosion noise for effect, along with some childish giggling. Dipper buckles up as the truck drives in reverse to exit the parking space. He closes his eyes and rests his elbow on the door, propping his head into his open palms. The truck travels forward and jets out of the McDonald's parking lot towards the center of the city.

"How was your shift?"

Dipper opens his eyes and glances towards the driver. "Same old, same old." He sighs. His attention shifts back to the window as they drive by newer apartment complexes.

He feels a hand gently touch his shoulder. "I was going to wait until Dinner to tell you the good news…" Dipper cocks his head over to the driver's seat, where Wendy Corduroy switches her focus from the road to his eyes. "Our secretary quit today, so I put in a good word with the boss." Dipper's eyes light up. "He said that I can bring you in for an interview next week." Wendy gleams as she returns to watching the road. "The firm might be able to help you finance getting your bachelors at Portland State. Then you'd be in good position to take a Data Analyst job in two years when Tammy retires." Wendy turns the steering wheel while Dipper sits in shock, unable to find the words to express his gratitude.

"Thanks, Wendy." He manages to choke out. Wendy reaches down with her hand and intertwines her fingers with his. Dipper clasps his fingers over hers and gently massages the back her hand. There's complete silence in the truck for the next three minutes. A joyous aura fills the vehicle, enhanced by the Thanksgiving holiday.

Wendy's truck approaches the street Dipper's apartment is on. Three more blocks and he would rush upstairs, quickly pack his bag with clothes for the night, and be off to Wendy's cabin in the woods for Thanksgiving with just her and Lilly.

The truck pushes forward on streets yet to be scraped by snow plows. Dipper glances out the window at the corner convenience store that he frequents every weekend to purchase beer. His eyes grow wide as he stares at a man standing awkwardly in front of the door to the shop. The man stares back and flashes a half-grinned smile at the truck. It's the same homeless man from the night before.

"Stop the truck." Dipper instructs softly. He turns his head as far as he can to keep sight of the man.

Wendy peers over at Dipper in confusion. "What, why?" She removes her hand from Dipper's grasp and places it back on the wheel.

Dipper points back at the store. "That homeless man, I offered him help yesterday, and he just walked out." Dipper completely turns around in his seat. He glares at the man, who taunts him through the back window of the truck with his wretched smile.

Wendy glances up at the rear-view mirror. "What man?" Now suspicious of Dipper, she raises a brow.

"Stop the truck!" Dipper shouts. Wendy slams on the breaks, causing the truck to skid to a halt. Dipper unbuckles and pushes through the door. He ignores the blast of bitter winter air as he slides towards the convenience store on the ice covered sidewalk. His legs grow weak as he nears the corner. After a few more steps, he stops in vain. The man is gone.

Wendy's red truck backs up to where Dipper stands. The front passenger window rolls down, exposing a pissed off Wendy. Dipper shields himself from an incoming open backpack as Wendy throws the bag out of the car. "I cannot believe you. You told me you quit!" She chokes. Wendy's face grows red to match her faded ginger locks. Dipper opens his mouth to rebuttal. "Save it!" She smacks her fists on the steering wheel in distress. "You know what that stuff does to people!" She shakes her head with disdain, and runs her hands through her hair. Dipper steps over the spilled contents of his backpack and attempts to open the car door, but Wendy locks it before he can. "When are you going to grow up?" She pushes herself back in her seat and stares at the ceiling of the truck. A tear drips down her cheek and falls onto her tartan patterned sweater. "I'm going to Seattle to see Nate for Thanksgiving, because at the moment he's as close to a father figure as Lilly's going to get." Wendy shifts the vehicle into drive and stares at the floor before turning to Dipper one last time. "How can I get married to someone who can't help raise a child, let alone himself?" The car window rolls up and Wendy speeds off, leaving Dipper gaping in disbelief.

Dipper pivots back towards the direction of the convenience store. He glues his mouth shut and bites the inside of his lip while he bends down and stuffs his loose belongings back into his bag. He slings the knapsack over his shoulder, springs to his feet, and stomps across the street. He approaches the door and grabs the cold metal handle. He pulls, but the door won't budge. He looks up and notices the lights are off inside, as well as the _Closed for Thanksgiving_ sign hanging chest-high in front of him.

Dipper glances down both streets. They are barren. Only the snow drifts off the flat rooftops and onto the street below. He smacks his fist on the vinyl siding of the store in anguish. A mountain of snow cascades off the roof above, covering Dipper in two feet of white rubble. He punts the snow in front of him and furiously brushes the cold flakes off his brown hair. Dipper angrily swipes the snow off his clothes and backpack while he treads the remaining two blocks to his apartment.

He stomps his way up three flights of wooden stairs to the top floor of the building. The walls in the stairwell were sky blue at some point, but a plethora of white splotches stain the walls. Dipper excavates in his pocket for his keys. Unlocking the door, he steps into his apartment and is greeted by a cool draft. He slams the door behind him and throws off his shoes. He moseys over to the thermostat and reads the temperature in the apartment. _10°C._ He flicks the switch twice to turn the heat off and on again. He listens for the usual kick and bang of the furnace, but it never arrives. Dipper leans his forehead against the wall and thumps it repeatedly in desolation. After five or six smacks, he steadies himself and traipses over to his kitchen. A pizza box filled with pieces of crust lies open on his counter next to numerous quarter-filled glasses of water, and at least a dozen empty beer cans. Pots and pans lie in disarray on the stove while rotten and dried food rests inside, caked to each saucepan. On the counter between the stove and the fridge is a mountain of unopened mail and bills. Dipper reaches for the fridge handle and pauses. He redirects his hand to a picture that is scotch-taped to the otherwise barren and old white refrigerator. He shakes his head and grits his teeth. His fist closes and he quickly finds himself crumpling a picture of him, Wendy, and a baby Lilly that was taken during a trip to Mount Rushmore. That vacation was Dipper's one year anniversary present for getting out of the hospital. Dipper clenches his eyes shut and chucks the photo across the room. It lands softly into his left shoe. He yanks the fridge open and shoves aside open takeout containers and more empty beer cans. He stretches towards the back of the darkened shelf and finds nothing but more cans vacant of watered down beer. He takes an almost empty half gallon jug of expired milk and chucks the ambient temperature container at the garbage can. Dipper plods over to his shoes, slips them on, and leaves his apartment without uttering a word.

He trudges through the snow for four blocks. The cold wind nips at his uncovered face, an annoying lump bothers his left sole, and the idea of Wendy rushing off to see her ex bothers Dipper with every step. Dipper reaches his usual pub, _The Parallax Tavern,_ where he is a household name to each and every one of the bartenders. He pushes on the door, but it doesn't budge. He stares at the neon red open sign that usually flashes a bright red. Today it is off. No light emanates from the halogen bulbs.

Dipper takes a deep breath and scans around. He spots a bar down the street with light shining through the glass and lumbers over to it like a mosquito would during a hot summer night. He glances up at the sign above the bar. _The PEN Bar._ He thinks the name sounds peculiar, but one glance through the window at the rows upon rows of glass bottles is enough for him to remove all doubt and push through the unlocked door.

Dipper casually strolls over to the counter and hops onto the bar stool. The bartender is absent for the moment. Dipper figures they're in the bathroom, so he taps his fingers on the laminate wood counter and examines the interior while he waits. The first thing he notices is that the place is completely unoccupied with customers. Each booth, four person table, and every other bar stool next to him is unfilled. He glances at the large paintings and license plates hanging on the walls around him. An elegant white fountain sits in the corner, splashing water into the bowl underneath the spout. He turns his attention back to the bar and spies a signed baseball in the foreground of a Chicago Cubs banner, presumably from the Cubs 2018 World Series Championship. Five minutes pass while Dipper waits within the conflicting badass and elegant vibes of the bar. Becoming irritated, he knocks on the counter and yells out to see if anyone is around.

A bottle hits the floor with a thud in the back room and it echoes over to Dipper. He peers his head over the bar counter when a coughing fit ensues in the backroom. He catches the glimpse of a sky blue dress and immediately sits upright in his stool. A gorgeous blonde haired woman, no older than Dipper, steps out of the back with a confused expression on her face. "How did you get in here?" She points at Dipper as she hesitantly stops midpoint between him and the back room.

"The door." Dipper says flatly with exhaustion and sheer annoyance. "I'll take a double of Jameson, on the rocks." He adds while he taps his fingers impatiently on the counter.

"Sorry sir, we're closed. It's Thanksgiving, go spend it with your family." The woman crosses her arms in a bratty manner and starts walking backwards to return to her activities in the back room.

Dipper pushes himself off the stool and points directly at her. "You may want to lock your door next time." He spews angrily. Dipper brushes his brown hair back in distress and turns away from the owner of the bar.

"Wait!" She rushes to the end of the counter and opens a swinging door that connects the seating area to the area behind the bar. The woman jumps in front of Dipper and places a hand on his chest to stop him in his tracks. "Dipper Pines?" She reaches her hand up to his forehead and lifts his semi-greasy hair, exposing his big dipper birthmark.

"Yeah…" Dipper pushes her hand away and takes a step back, half in fear and half in confusion. He glances around for some sort of weapon, just in case this woman is mad. He thinks his best option is a bar stool, so he slowly inches towards the closest one on his left.

The woman laughs hysterically. After a few seconds she smiles and shakes her head in disbelief. "It's me. Pacifica Northwest." Dipper stands as still as a statue, unable to comprehend what is going on. Pacifica chuckles while stepping forward to embrace him. Dipper backs away.

Dipper hyperventilates. "This can't be happening." He snags a bar stool and swings it in the air. Pacifica dodges the first swipe and leaps back. "I'll kill you Bill!" He grits through his teeth. Dipper raises the stool over his skull and prepares to throw it, when out of the corner of his eye, he spies the homeless man standing across the street gazing right at him. Dipper's limbs grow weak and the stool falls harmlessly to the wooden floor next to him. He wanders forward in a trance, as if she isn't there, and heads towards the door.

Pacifica clutches onto the counter and avoids Dipper as he walks by. Terrified, she spins to the window and stares at the brick wall of the building across the street. Pacifica leans over the bar counter, grabs a bottle of Jack, and follows Dipper from behind. Dipper steps to the door and reaches his hand out to pull it open. Pacifica elevates the glass container. Dipper's wraps his fingers around the metal handle. "I'm sorry Dipper." Pacifica smashes the bottle on the back of his skull. Whiskey cascades to the floor with glass shards. Dipper loses his balance.

As his vision blacks out, the homeless man limps away.


End file.
